87428-52-2Relevant articles and documents
One-Pot Enzymatic-Chemical Cascade Route for Synthesizing Aromatic α-Hydroxy Ketones
Wang, Lei,Song, Wei,Wang, Binju,Zhang, Yan,Xu, Xin,Wu, Jing,Gao, Cong,Liu, Jia,Chen, Xiulai,Chen, Jinghua,Liu, Liming
, p. 2808 - 2818 (2021/03/15)
2-Hydroxyacetophenone (2-HAP) is an important building block for the production of a series of natural products and pharmaceuticals; however, there is no safe, efficient, and economical method for 2-HAP synthesis. Here, a one-pot enzymatic-chemical cascade route was designed for synthesizing 2-HAP based on retrosynthetic analysis. First, a spontaneous proton-transfer reaction was designed using a computational simulation that enabled 2-HAP synthesis from the isomer 2-hydroxy-2-phenylacetaldehyde. A route for 2-hydroxy-2-phenylacetaldehyde synthesis was then constructed by introducing the unnatural substrate glyoxylic acid into a C-C ligation reaction catalyzed by Candida tropicalis pyruvate decarboxylase. Assembly and optimization of this enzymatic-chemical cascade route resulted in a final yield of 92.7%. Furthermore, stereospecific carbonyl reductases were introduced to construct a synthetic application platform that enabled further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method of cascading spontaneous chemical and enzymatic reactions to synthesize chemicals offers insight into avenues for synthesizing other valuable chemicals.
Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
Pan, Ting,Gao, Xing,Yang, Sen,Wang, Lan,Hu, Yimin,Liu, Min,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
supporting information, p. 5750 - 5754 (2021/08/16)
In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).
Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes
Chen, Yuehua,Deng, Hao,Gao, Xing,Guo, Hongchao,Jiang, Feng,Wang, Wei,Wu, Yongjun,Zhu, Dongyu
supporting information, p. 7158 - 7163 (2020/10/02)
A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.
